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A2 A1 A4 A3 A6 A5 A8 A7 .

A10 A9 A12 A11 A14 A13 A16 A15 .

A18 A17 A20 A19 A22 A21 A24 A23 .

A26 A25 A28 A27 A30 A29 .

The racemic mixture of a chiral compound. The configuration at a chirality center as specified using the Cahn–Ingold–Prelog sequence rules. . Enantiomers have opposite configurations at all chirality centers. An optically active substance that rotates the plane of polarization of plane–polarized light in a left–handed (counterclockwise) direction. Compounds that have the same molecular formula but different structures. One of two identical atoms in a compound whose replacement leads to an R chirality center.Stereoisomers of a chiral substance that have a mirror–image relationship. One of two identical atoms in a compound whose replacement leads to an S chirality center. Diastereomers that differ in configuration at only one chirality center but are the same at all others.

sp2– hybridized atom. Molecules w/ a plane of symmetry are achiral. An older. Absolute configurations are specified verbally by the Cahn–Ingold– Prelog R. sp2– hybridized atom. One of two faces of a planar. One of two faces of a planar.S convention. The configuration at a chirality center as specified using the Cahn–Ingold–Prelog sequence rules. A substance that rotates the plane of polarization of plane–polarized light.A compound that contains chirality centers but is nevertheless achiral because it contains a symmetry plane. Optical isomers are isomers that have a mirror– image relationship. alternative name for enantiomers. A plane that bisects a molecule so one half of the molecule is the mirror image of the other half. The exact 3-D structure of a chiral molecule. .

The plane of polarization rotates when the light passes through a solution of a chiral substance. A molecule is achiral if it has a plane of symmetry and is thus superimposable on its mirror image. Chiral molecules have no plane of symmetry & are not superimposable on their mirror image. A molecule that can be converted from achiral to chiral in a single chemical step. An atom in a compound that can be converted into a chirality center by changing one of its attached substituents. A series of rules for assigning relative priorities to substituent groups on a double–bond carbon atom or on a chirality center. Chiral surroundings or conditions in which a molecule resides. A mixture consisting of equal parts (+) and (−) enantiomers of a chiral substance. Having a lack of handedness.Ordinary light w/ EM waves oscillating in a single plane. A chiral molecule has 2 forms: right–handed and left–handed. The most common cause of chirality is having a carbon atom w/ 4 different substituents. . Having handedness.

The optical rotation of a chiral compound under standard conditions. The three– dimensional arrangement of atoms bonded to a chirality center. butane and 2–methylpropane are constitutional isomers. An atom (usually carbon) that is bonded to four different groups. For example.The process by which a racemic mixture is separated into its two pure enantiomers. A word used to describe an optically active substance that rotates the plane of polarization of plane–polarized light in a right–handed (clockwise) direction. . A series of rules for assigning relative priorities to substituent groups on a double–bond carbon atom or on a chirality center. Isomers that have their atoms connected in a different order. Isomers that have their atoms connected in the same order but have different three– dimensional arrangements. The term stereoisomerinc ludes both enantiomers and diastereomers.

diastereomers have the same configuration at one or more chirality centers but differ at other chirality centers.A plane that bisects a molecule such that one half of the molecule is the mirror image of the other half. such as dipole–dipole forces. The ability of an atom to attract electrons in a covalent bond. A weak attraction between a hydrogen atom bonded to an electronegative atom and an electron lone pair on another electronegative atom. Non–mirror–image stereoisomers.. and hydrogen bonds. A naturally occurring organic base. The anion that results from deprotonation of a Brønsted–Lowry acid. One of a variety of nonbonding interactions between molecules. Electronegativity increases across the periodic table from right to left and from bottom to top. with one of the oxygens also bonded to carbon. dispersion forces. Molecules containing a plane of symmetry are achiral. such as morphine. . A compound that contains a phosphorus atom bonded to four oxygens. The product that results from protonation of a Brønsted–Lowry base.

Steric strain causes greater stability of trans versus cis alkenes and greater stability of equatorially substituted versus axially substituted cyclohexanes.. An aliphatic cyclic hydrocarbon such as a cycloalkane or cycloalkene. .. The covalent bond formed by sideways overlap of atomic orbitals. A mathematical expression that defines the behavior of an electron in an atom. The strain energy caused by a steric interaction between axial groups three carbon atoms apart in chair cyclohexane. The total of protons plus neutrons in an atom. A means of assessing the energy of a substituted cycloalkane by totaling the steric interactions present in the molecule.A solution to the wave equation for defining the behavior of an electron in an atom. A covalent bond formed by head–on overlap of atomic orbitals. The square of the wave function defines the shape of an orbital. strain on a molecule when 2 groups try to occupy the same space. The number of protons in the nucleus of an atom. The average mass number of the atoms of an element. A molecular orbital that is higher in energy than the atomic orbitals from which it is formed...

8 kJ/mol steric strain. (CH3)3CCH2−. a secondary site has two organic substituents. The term stereoisomer includes enantiomers and diastereomers.2– dimethylpropyl group. For any acid HA. a tertiary site has three. butane and 2–methylpropane are constitutional isomers.Isomers that have their atoms connected in a different order. A primary site has one organic substituent attached to it. and a quaternary site has four. The 2. The angle between two bonds on adjacent carbons as viewed along the C– C bond. the acidity constant is given by the expression Ka = [H3O+][A-] / [HA] Compounds that have the same molecular formula but different structures. For example. A measure of acid strength in water. This conformation has 3. . The conformation of butane in which the two methyl groups lie 60° apart as viewed in a Newman projection. Isomers w/ atoms connected in the same order but have different 3-D arrangements. describes the substitution pattern at a specific site.

l form Enantiomers pro–R configuration Epimers pro–S configuration Isomers R configuration Levorotatory .d.

Re face Meso compound S configuration Optical isomers Si face Optically active Absolute configuration Plane of symmetry .

Achiral Plane–polarized light Cahn–Ingold–Prelog  sequence rules Prochiral Chiral Prochirality center Chiral environment Racemate .

Chirality center Resolution Configuration Sequence rules Constitutional isomers Specific rotation. [α]D Dextrorotatory Stereoisomers .

Diastereomers Symmetry plane Conjugate acid. Conjugate  base Electronegativity Hydrogen bond Alkaloid Noncovalent interaction Organophosphate .

 Atomic number. Sigma (σ) bond Wave function.Pi (π) bond.3–Diaxial interaction . Z Antibonding MO Alicyclic Conformational analysis Steric strain 1. A. Mass  number. Wave  equation Atomic mass.

 tertiary.  quaternary Stereoisomers Dihedral angle . secondary. Ka Constitutional isomers Gauche conformation Isomers Neopentyl group Primary.Acidity constant.

The configuration at a chirality center as specified using the R configuration Cahn–Ingold–Prelog sequence rules. Absolute configurations are specified verbally by the Cahn– Ingold–Prelog R. Chiral surroundings or conditions in which a molecule Chiral environment resides. A molecule is achiral if it has a Achiral plane of symmetry and is thus superimposable on its mirror image. one right–handed and one left–handed.l form pro–R configuration . sp2–hybridized atom. One of two identical atoms in a compound whose pro–S configuration replacement leads to an S chirality center. For example. Chiral Having handedness.Sconvention. Re face The configuration at a chirality center as specified using the S configuration Cahn–Ingold–Prelog sequence rules. Having a lack of handedness. Si face Absolute configuration The exact threedimensional structure of a chiral molecule. The three–dimensional arrangement of atoms bonded to a Configuration chirality center.The racemic mixture of a chiral compound. One of two identical atoms in a compound whose replacement leads to an R chirality center. d. The most common cause of chirality in a molecule is the presence of a carbon atom that is bonded to four different substituents. Chiral molecules are those that do not have a plane of symmetry and are therefore not superimposable on their mirror image. Constitutional isomers Isomers that have their atoms connected in a different order. Enantiomers have opposite configurations at all chirality centers. One of two faces of a planar. butane and 2–methylpropane are constitutional isomers. One of two faces of a planar. Diastereomers that differ in configuration at only one chirality Epimers center but are the same at all others. diastereomers have the Diastereomers same configuration at one or more chirality centers but differ at other chirality centers. Cahn–Ingold–Prelog  A series of rules for assigning relative priorities to substituent groups on a double–bond carbon atom or on a chirality sequence rules center. A chiral molecule thus exists in two forms. sp2–hybridized atom. Non–mirror–image stereoisomers. A word used to describe an optically active substance that Dextrorotatory rotates the plane of polarization of plane–polarized light in a right–handed (clockwise) direction. Stereoisomers of a chiral substance that have a mirror–image Enantiomers relationship. An atom (usually carbon) that is bonded to four different Chirality center groups.

An older. The process by which a racemic mixture is separated into its two pure enantiomers.Isomers Levorotatory Meso compound Optical isomers Optically active Plane of symmetry Plane–polarized light Prochiral Prochirality center Racemate Resolution Sequence rules Specific rotation. A plane that bisects a molecule such that one half of the molecule is the mirror image of the other half. Ordinary light that has its electromagnetic waves oscillating in a single plane rather than in random planes. [α]D Stereoisomers Symmetry plane Compounds that have the same molecular formula but different structures. The optical rotation of a chiral compound under standard conditions. alternative name for enantiomers. . An atom in a compound that can be converted into a chirality center by changing one of its attached substituents. The term stereoisomerincludes both enantiomers and diastereomers. Optical isomers are isomers that have a mirror–image relationship. Isomers that have their atoms connected in the same order but have different three–dimensional arrangements. A plane that bisects a molecule such that one half of the molecule is the mirror image of the other half. A mixture consisting of equal parts (+) and (−) enantiomers of a chiral substance. Molecules containing a plane of symmetry are achiral. A compound that contains chirality centers but is nevertheless achiral because it contains a symmetry plane. The plane of polarization is rotated when the light is passed through a solution of a chiral substance. A series of rules for assigning relative priorities to substituent groups on a double–bond carbon atom or on a chirality center. A molecule that can be converted from achiral to chiral in a single chemical step. An optically active substance that rotates the plane of polarization of plane–polarized light in a left–handed (counterclockwise) direction. A substance that rotates the plane of polarization of plane– polarized light. Molecules containing a plane of symmetry are achiral.

Boat cyclohexane A conformation of cyclohexane that bears a slight resemblance to a boat. Bridgehead atom An atom that is shared by more than one ring in a polycyclic molecule. Bent bonds are highly strained and highly reactive.The strain energy caused by a steric interaction between axial groups three carbon atoms apart in chair cyclohexane. Stereoisomers Isomers that have their atoms connected in the same order but have different three–dimensional arrangements. Boat cyclohexane has no angle strain but has a large number of eclipsing interactions that make it less stable than chair cyclohexane (chair form is the lowest-energy conformation of the molecule). The term stereoisomerincludes both enantiomers and diastereomers. Conformational  A means of assessing the energy of a substituted cycloalkane by totaling the steric interactions present analysis in the molecule. A computer–based method for calculating the Molecular  minimum–energy conformation of a molecule. Angle strain is particularly important in small–ring cycloalkanes. An aliphatic cyclic hydrocarbon such as a cycloalkane Alicyclic or cycloalkene. An alkane that contains a ring of carbons. The effect of a ring–flip is to convert an axial substituent into an equatorial substituent. Cis–trans isomers Stereoisomers that differ in their stereochemistry about a double bond or ring. mechanics Polycyclic  A compound that contains more than one ring. compound Ring–flip A molecular motion that converts one chair conformation of cyclohexane into another chair conformation. Bent bonds The bonds in small rings such as cyclopropane that bend away from the internuclear line and overlap at a slight angle. rather than head–on. Cycloalkane Equatorial bond A bond to cyclohexane that lies along the rough equator of the ring.3–Diaxial  interaction . Angle strain The strain introduced into a molecule when a bond angle is deformed from its ideal value. 1. where it results from compression of bond angles to less than their ideal tetrahedral values.

Steric strain Twist–boat  conformation The strain imposed on a molecule when two groups are too close together and try to occupy the same space. . Steric strain is responsible both for the greater stability of trans versus cis alkenes and for the greater stability of equatorially substituted versus axially substituted cyclohexanes. A conformation of cyclohexane that is somewhat more stable than a pure boat conformation.

and bonds radiating from the edge of the circle are attached to the rear carbon.2–dimethylpropyl group. Hydrocarbon Compounds that have the same molecular formula but Isomers different structures. and the carbons are indicated by a circle. Conformer Isomers that have their atoms connected in a different Constitutional  order. assuming that rotation around single bonds is frozen. Propane. The three–dimensional shape of a molecule at any given instant.8 kJ/mol steric strain. devised by the International Union of Pure and Applied Chemistry. The geometric arrangement around a carbon–carbon single bond in which the two largest substituents are 180° apart as viewed in a Newman projection. A compound that contains only carbon and hydrogen. The carbon–carbon bond is viewed end–on. nomenclature Neopentyl group The 2. The conformation of butane in which the two methyl Gauche  groups lie 60° apart as viewed in a Newman projection. for example. alkene. conformation This conformation has 3. . For example. has the condensed structure CH3CH2CH3. Functional group An atom or group of atoms that is part of a larger molecule and that has a characteristic chemical reactivity. (CH3)3CCH2−. IUPAC system of  Rules for naming compounds. Conformation Newman  projection A means of indicating stereochemical relationships between substituent groups on neighboring carbons. A conformational isomer. Bonds radiating from the center of the circle are attached to the front carbon. or alkyne. Eclipsing strain is also called torsional strain. butane and 2–methylpropane are isomers constitutional isomers. The partial structure that remains when a hydrogen atom is removed from an alkane.Aliphatic Alkyl group Anti  conformation Condensed  structure A nonaromatic hydrocarbon such as a simple alkane. The angle between two bonds on adjacent carbons as Dihedral angle viewed along the C–C bond. A shorthand way of writing structures in which C−H and C−C bonds are understood rather than shown explicitly. Eclipsed  The geometric arrangement around a carbon–carbon conformation single bond in which the bonds to substituents on one carbon are parallel to the bonds to substituents on the neighboring carbon as viewed in a Newman projection. Eclipsing strain The strain energy in a molecule caused by electron repulsions between eclipsed bonds.

The term stereoisomerincludes both enantiomers and diastereomers. A common name for alkanes. Normal alkanes are denoted by the suffix n. Alkanes are saturated. Isomers that have their atoms connected in the same Stereoisomers order but have different three–dimensional arrangements. Torsional strain is also called eclipsing strain. Steric strain The strain imposed on a molecule when two groups are too close together and try to occupy the same space. Terms used to describe the substitution pattern at a specific site. A manner of representing stereochemistry that uses a Sawhorse  stick drawing and gives a perspective view of the structure conformation around a single bond. A molecule that has only single bonds and thus can’t Saturated undergo addition reactions.Normal alkane A straight–chain alkane. Paraffin Primary. Stereochemistry The branch of chemistry concerned with the three– dimensional arrangement of atoms in molecules. as in n−C4H10 (n–butane).  secondary. A generalized abbreviation for an organic partial R group structure.  quaternary . Steric strain is responsible both for the greater stability of trans versus cis alkenes and for the greater stability of equatorially substituted versus axially substituted cyclohexanes. a secondary site has two organic substituents. Torsional strain The strain in a molecule caused by electron repulsion between eclipsed bonds. as opposed to a branched alkane. A primary site has one organic substituent attached to it. a tertiary site has three. but alkenes are unsaturated. and a quaternary site has four.  tertiary.

  Conjugate base Debye. such as dipole–dipole forces. A noncovalent electrostatic interaction between polar molecules. 1 D = 3. All nucleophiles are Lewis bases. Ka A measure of acid strength in water. The unit for measuring dipole moments.  Brønsted–Lowry base Conjugate acid. The negative common logarithm of the Ka. H+) to a base. Water–loving. dispersion forces. The anion that results from deprotonation of a Brønsted–Lowry acid. attracted to water. A noncovalent interaction between molecules that arises because of constantly changing electron distributions within the molecules.. Noncovalent interaction One of a variety of nonbonding interactions between molecules. A dipole moment arises when the centers of mass of positive and negative charges within a molecule do not coincide. Lewis base A substance with a vacant low–energy orbital that can accept an electron pair from a base. Alkaloid Brønsted–Lowry acid. An individual Lewis structure of a resonance hybrid. A substance that donates a hydrogen ion (proton. For any acid HA. The product that results from protonation of a Brønsted–Lowry base. Resonance form . and hydrogen bonds. Electronegativity increases across the periodic table from right to left and from bottom to top.336 × 10-30 coulomb meter (C · m). All electrophiles are Lewis acids. The electronattracting or electron–withdrawing effect transmitted through σ bonds. used to pKa express acid strength. D Dipole moment. A substance that accepts H+ from an acid. not attracted to water. The ability of an atom to attract electrons in a covalent bond. The unsymmetrical distribution of electrons in a Polarity molecule that results when one atom attracts electrons more strongly than another. the acidity constant is given by the expression Ka = [H3O+][A-] / [HA] A naturally occurring organic base.  Hydrophobic Inductive effect Lewis acid. such as morphine.. Water–fearing. A weak attraction between a hydrogen atom bonded to an electronegative atom and an electron lone pair on another electronegative atom. Electronegative elements have an electron–withdrawing inductive effect. A measure of the net polarity of a molecule.Acidity constant. μ Dipole–dipole force Dispersion force Electronegativity Hydrogen bond Hydrophilic. A substance that donates an electron lone pair to an acid..

.Van der Waals forces Intermolecular forces that are responsible for holding molecules together in the liquid and solid states.

An alternative name for bond Bond  dissociation energy. Hund’s rule If two or more empty orbitals of equal energy are available. The total of number. The Atomic  number of protons in the nucleus of an number.sp Hybrid  orbital A hybrid orbital derived from the combination of an s and a p atomic orbital. Condensed  A shorthand way of writing structures in which C−H and C−C bonds are structure understood rather than shown explicitly. until all are half–full. A... for example. Antibonding  A molecular orbital that is higher in energy than the atomic orbitals from MO which it is formed.  protons plus neutrons in an atom. The two sp orbitals that result from hybridization are oriented at an angle of 180° to each other. Ground state The most stable. A list of the orbitals occupied by Electron  configuration electrons in an atom.  The average mass number of the Mass  atoms of an element. has the condensed structure CH3CH2CH3. strength Bonding MO A molecular orbital that is lower in energy than the atomic orbitals from which it is formed. . one electron occupies each. Z atom. Propane. 3 sp  Hybrid  A hybrid orbital derived by combination orbital of an s atomic orbital with three p atomic orbitals. The three sp2 hybrid orbitals that result lie in a plane at angles of 120° to each other. sp2 Hybrid  orbital A hybrid orbital derived by combination of an s atomic orbital with two p atomic orbitals. The four sp3 hybrid orbitals that result are directed toward the corners of a regular tetrahedron at angles of 109° to each other. Atomic mass. with their spins parallel. lowest–energy electron configuration of a molecule or atom.

A covalent bond formed by head–on overlap of bond atomic orbitals. are strongly directed and form stronger bonds than atomic orbitals do. principle Pi (π) bond. A mathematical expression that defines the behavior of an electron in an atom. Organophosp A compound that contains a hate phosphorus atom bonded to four oxygens. such as the sp3. Kekulé  A method of representing molecules in structure. perpendicular to the axis of the orbital..  defining the behavior of an electron in Wave  an atom. No more than two electrons can occupy Pauli  the same orbital. The square of the wave equation function defines the shape of an orbital. Node A surface of zero electron density within an orbital. sp2. and sp hybrids of carbon. Hybrid orbitals. Wave  A solution to the wave equation for function. and those two must exclusion  have spins of opposite sign.Hybrid orbital An orbital derived from a combination of atomic orbitals. A Line–bond  representation of a molecule showing structure covalent bonds as lines between atoms.  which a line between atoms indicates a Lewis  bond.  The covalent bond formed by sideways Sigma (σ)  overlap of atomic orbitals. Atoms of the same element that have Isotopes different mass numbers. with one of the oxygens also bonded to carbon. Skeletal  A shorthand way of writing structures in structure which carbon atoms are assumed to be at each intersection of two lines (bonds) and at the end of each line. A representation of a molecule structure.. For example. ...  showing valence electrons as dots. a p orbital has a nodal plane passing through the center of the nucleus. A neutral collection of atoms held Molecule together by covalent bonds.

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